Fungicidal derivatives of carbocyclic anilides

ABSTRACT

Fungicidal derivatives of carboxyclic anilides of the formula ##STR1## in which X represent optionally alkyl-substituted cycloalkyl or optionally alkyl-substituted cycloalkenyl, 
     Hal represents halogen, and 
     Y 1 , Y 2  and Y 3  independently of one another represent hydrogen, halogen, optionally halogen-substituted alkyl, optionally halogen-substituted alkoxy or optionally halogen-substituted alkylthio, and 
     Z represents the groups COOR 2  or COR 1 , where 
     R 1  and R 2  are identical or different and represent optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl and optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted phenylalkyl or substituted phenoxyalkyl.

The present invention relates to new cycloalkyl- orcycloalkenylcarboxanilides, to a process for their preparation, and totheir use for combating pests, in particular fungi.

It is known that certain carbamates have good fungicidal properties (cf.EP Pat. No. 293,718).

Furthermore, many carboxanilides having a fungicidal action are known,in particular those having a powerful action againstbenzimidazole-tolerant plant pathogens (cf. EP Pat. No. 117,024, EP Pat.No. 125,901, EP Pat. No. 100,615).

New cycloalkyl or cycloalkenyl-carboxanilides of the general formula (I)##STR2## in which

X represents optionally alkyl-substituted cycloalkyl or optionallyalkyl-substituted cycloalkenyl,

Hal represents halogen, and

Y¹, Y² and Y³ independently of one another represent hydrogen, halogen,optionally halogen-substituted alkyl, optionally halogen-substitutedalkoxy or optionally halogen-substituted alkylthio, and

Z represents the groups COOR² or COR¹, where

R¹ and R² are identical or different and represent optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl,polyalkoxyalkyl and optionally substituted cycloalkyl, optionallysubstituted phenyl, optionally substituted phenylalkyl or substitutedphenoxyalkyl, have been found.

The substituted cycloalkyl- or cycloalkenylcarboxanilides of the formula(I) contain one or more centers of asymmetry and can therefore be in theform of diastereomers or mixtures of diastereomers, obtained in varyingratios. They are mainly obtained in the form of racemates.

Furthermore, it has been found that the new substituted cycloalkyl- orcycloalkenylcarboxanilides of the formula (I) ##STR3## in which

X is optionally alkyl-substituted cycloalkyl or optionallyalkyl-substituted cycloalkenyl,

Hal is halogen and

Y¹, Y² and Y³ are identical or different and represent hydrogen,halogen, optionally halogen-substituted alkyl, optionallyhalogen-substituted alkoxy or optionally halogen-substituted alkylthio,and

Z represents the groups COOR² or COR¹, where

R¹ and R² are identical or different and represent optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl,polyalkoxyalkyl and optionally substituted cycloalkyl, optionallysubstituted phenyl, optionally substituted phenylalkyl or substitutedphenoxyalkyl,

are obtained when aminophenols of the formula (II) ##STR4## in which

Hal, Y¹, Y² and Y³ have the abovementioned meanings, are reacted, in afirst reaction step, with carboxylic acid derivatives of the formula(III) ##STR5##

in which

X has the abovementioned meaning and

Hal¹ represents halogen, preferably chlorine, or represents a leavinggroup customary in acylation reactions, preferably an activating esterradical, if appropriate in the presence of an acid acceptor and ifappropriate in the presence of a solvent or diluent, and these resultingintermediates of the formula (IV) ##STR6## in which

X, Y¹, Y², Y³ and Hal have the abovementioned meanings, are reacted in asecond step with carbonyl derivatives of the formula (V)

    Z--Hal.sup.2

in which

Z has the abovementioned meaning and

Hal² represents halogen, preferably chlorine, or a leaving groupcustomary in acylation reactions, preferably an activating esterradical,

if appropriate in the presence of an acid acceptor and if appropriate inthe presence of a solvent or diluent.

Finally, it has been found that the substituted cycloalkyl- orcycloalkenyl-carboxanilides of the formula (I) and (IVa) have, interalia, a powerful fungicidal activity. The new compounds can also be usedwith other known, highly-effective compounds in synergistic mixtures.

Within the scope of the present invention, the substituents preferablyhave the following meanings:

Unless stated otherwise, halogen can denote fluorine, chlorine, bromineand iodine, preferably fluorine, chlorine and bromine.

Alkyl, alkoxy and alkylthio represent radicals which have 1-8,preferably 1-6 and particularly preferably 1-4 carbon atoms per alkylunit, for example methyl, ethyl, n- and iso-propyl, n-, sec-, iso- andtert.-butyl, pentyl, n-hexyl or iso-hexyl, methoxy, ethoxy, n- andiso-propoxy, n-, sec-, iso- and tert.-butoxy, pentoxy and hexoxy,methylthio, ethylthio, n- and iso-propylthio, n-, sec.-, iso- andtert.-butylthio, pentylthio and hexylthio.

Halogenoalkoxy or halogenoalkylthio generally represents astraight-chain or branched hydrocarbon radical which has 1-6 carbonatoms and 1-9 identical or different halogen atoms and which is bondedvia oxygen, or sulphur, respectively. Preferred radicals are thosehaving 1-4 carbon atoms and 1-5 identical or different halogen atoms.Very particularly preferred radicals are those having 1 or 2 carbonatoms and 1-3 identical or different halogen atoms. The following may bementioned as examples: trifluoromethoxy, trichloromethoxy,difluorochloromethoxy, dichlorofluoromethoxy, difluoroethoxy,trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy,trifluoromethylthio, trichloromethylthio, difluorochloromethylthio,dichlorofluoromethylthio, difluoroethylthio, trifluoromethylthio andtetrafluoroethylthio.

Halogenoalkyl has the meaning of halogenoalkoxy, with the differencethat the oxygen is missing.

Cycloalkyl generally represents a cyclic hydrocarbon radical having 3-10carbon atoms. Radicals having 3-7 carbon atoms are preferred. Thefollowing may be mentioned as examples: cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl and cyclodecanyl.

The cycloalkyl radicals can be monosubstituted to polysubstituted.Substituents which may be mentioned are alkyl having 1-4 carbon atoms,halogen, halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identicalor different halogen atoms, alkoxy having 1 to 4 carbon atoms, hydroxyland alkylcarbonyloxy having 1 to 6 carbon atoms in the alkyl moiety.

Cycloalkenyl generally represents a cyclic hydrocarbon radical having5-10 carbon atoms.

Radicals having 5-7 carbon atoms are preferred. The following may bementioned as examples: cyclopentenyl, cyclohexenyl and cycloheptenyl.

The cycloalkenyl radicals can be monosubstituted to polysubstituted.Substituents which may be mentioned are alkyl radicals having 1-6 carbonatoms.

In this context, the preferred and particularly preferred meanings ofalkyl are those which have already been given further above.

Phenyl, phenylalkyl and substituted phenoxyalkyl generally representsphenyl, phenylalkyl and phenoxyalkyl, in which phenyl hydrogen atoms areoptionally replaced by one or more substituents Y¹ '-Y⁵ '. In thiscontext, Y¹ '-Y⁵ ' have the meaning of Y¹, Y² and Y³ as well as nitroand cyano.

Alkenyl generally represents a straight-chain or branched hydrocarbonradical having 2 to 8 carbon atoms and one or more, preferably one ortwo, double bonds. Lower alkenyl having 2 to 6 carbon atoms and onedouble bond is preferred. An alkenyl radical having 2 to 5 carbon atomsand one double bond is particularly preferred.

Formula (I) provides a general definition of the substituted cycloalkyl-or cycloalkenyl-carboxanilides according to the invention. Preferredcompounds of the formula (I) are those where

X represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl orcycloheptyl, each of which is optionally monosubstituted totetrasubstituted by identical or different substituents from the seriescomprising straight-chain or branched alkyl radicals having 1-4 carbonatoms, or represents cycloalkenyl having 5-7 ring members are optionallymonosubstituted to hexasubstituted by identical or differentsubstituents from the series comprising straight-chain or branched alkylradicals having 1-4 carbon atoms,

Hal represents fluorine, chlorine or bromine,

Y¹, Y² and Y³ are identical or different and represent hydrogen,fluorine, chlorine, bromine, straight-chain or branched alkyl having 1-4carbon atoms, straight-chain or branched alkoxy or alkylthio each having1-4 carbon atoms, or represent halogenoalkyl, halogenoalkoxy orhalogenoalkylthio each having 1-4 carbon atoms in the straight-chain orbranched alkyl moiety and having 1-5 identical or different halogenatoms.

Z represents COOR² or COR¹, where

R¹ and R² are identical or different and represent C₁ -C₈ -alkyl, C₂ -C₈-alkenyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy-C₁-C₄ -alkyl or C₁ -C₄ -alkylthio-C₁ -C₄ -alkyl, each of which isoptionally monosubstituted to nonasubstituted by halogen, or representC₃ -C₇ -cycloalkyl which is unsubstituted or monosubstituted topentasubstituted by identical or different substituents from the seriescomprising C₁ -C₄ -halogenoalkyl, halogen, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, hydroxyl and C₁ -C₆ -alkylcarbonyloxy, or represent phenyl-C₁-C₄ -alkyl which is unsubstituted or monosubstituted to pentasubstitutedin the phenyl moiety by identical or different substituents from theseries comprising Y¹ '-Y⁵ ', or represent phenoxyalkyl which isunsubstituted or monosubstituted to pentasubstituted in the phenylmoiety by identical or different substituents from the series comprisingY¹ '-Y⁵ ', where Y¹ '-Y⁵ ' have the meaning of Y¹ -Y³, NO₂ and cyano.

Particularly preferred compounds of the formula (I) are those where

X represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl orcycloheptyl, each of which is monosubstituted or disubstituted byidentical or different substituents from the series comprisingstraight-chain or branched alkyl radicals having 1-4 carbon atoms, orrepresents cyclopentenyl, cyclohexenyl or cycloheptenyl, each of whichis optionally monosubstituted or disubstituted by identical or differentsubstituents from the series comprising straight-chain or branched alkylradicals having 1-4 carbon atoms,

Y¹, Y² and Y³ are identical or different and represent hydrogen,fluorine, chlorine, bromine, methyl or trifluoromethyl, and

Hal represents fluorine, chlorine or bromine,

Z represents COOR² or COR¹, where

R¹ and R² are identical or different and represent C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy-C₁-C₄ -alkyl or C₁ -C₄ -alkylthio-C₁ -C₂ -alkyl, or represent C₃ -C₇-cycloalkyl which is unsubstituted or monosubstituted to trisubstitutedby identical or different substituents from the series comprisingfluorine, chlorine, bromine, C₁ -C₂ -alkyl, C₁ -C₂ -alkoxy or C₁ -C₆-alkylcarbonyloxy, or represent phenyl which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituentsfrom the series comprising nitro, cyano, fluorine, chlorine, bromine,methyl, trifluoromethyl, trifluoromethylthio, methoxy andtrifluoromethoxy, or represent phenyl-C₁ -C₂ -alkyl which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents from the series comprising nitro, cyano,fluorine, chlorine, bromine, methyl, trifluoromethyl,trifluoromethylthio, methoxy and trifluoromethoxy, or representphenoxy-C₁ -C₂ -alkyl which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents from the seriescomprising nitro, cyano, fluorine, chlorine, bromine, methyl,trifluoromethyl, trifluoromethylthio, methoxy and trifluoromethoxy.

Very particularly preferred compounds of the formula (I) are those where

X represents cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl,cyclohexenyl or cycloheptenyl, each of which is substituted in the 1- or1,3-position by methyl or ethyl and each of which is optionallyadditionally substituted by a further alkyl radical having 1-3 carbonatoms,

Hal represents fluorine, chlorine or bromine, and

Y¹, Y² and Y³ are identical or different and represent hydrogen,fluorine, chlorine, bromine or trifluoromethyl,

Z represents COOR² or COR¹, where R¹ and R² are identical or differentand represent C₁ -C₄ -alkyl, C₂ -C₅ -alkenyl, C₁ -C₄ -alkoxy-C₁ -C₄-alkyl or C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, or represent C₃-C₇ -cycloalkyl which is monosubstituted to trisubstituted by identicalor different substituents from the series comprising methoxy, fluorine,chlorine, bromine, methyl and C₁ -C₄ -alkylcarbonyloxy, or representphenyl which is monosubstituted to trisubstituted by identical ordifferent substituents from the series comprising nitro, cyano,fluorine, chlorine, bromine, methyl and methoxy, or representphenylmethyl which is monosubstituted to trisubstituted by identical ordifferent substituents from the series comprising nitro, cyano,fluorine, chlorine, bromine, methyl and methoxy.

If, for example, 2,6-dichloro-4-amino-phenol,1-methyl-1-chlorocarbonylcyclohexane and butyl chloroformate are used asstarting substances, the course of the reaction can be represented bythe following equation: ##STR7##

Formula (II) provides a general definition of the aminophenols requiredas starting substances for carrying out the process according to theinvention. In this formula (II), the radicals Hal and Y¹ -Y³ have themeanings already given in connection with the description of thecompounds of the formula (I) according to the invention. Most of thecompounds are known and can be prepared by analogous processes (cf."Methoden der organischen Chemie" ]Methods of Organic Chemistry],Houben-Weyl, Volume VI/1c, Phenols, Part 1, Georg Thieme Verlag,Stuttgart, 1976, and "Reaktionen der organischen Synthese" [Reactions inOrganic Synthesis], Cesare Ferri, p. 81, 89, 91, 97, 118, 120, 122, 124,126, 128, Georg Thieme Verlag, Stuttgart, 1978).

The 4-amino-2-chloro- or -2-bromo-6-trifluoromethylphenols are knownfrom Japanese Kokai Tokkyo Koho Jp Pat. No. 61/126055, and, for example4-amino-2,3,5,6-tetrafluorophenol, from Zh. Org. Khim. 10(9), 1923-1927(1974). The compounds of the formula (II A) ##STR8## in which

Y⁴ represents fluorine or chlorine, are a subject of EP-A-No. 293,718and are prepared for example from corresponding hydroxybenzoic acids ofthe formula (V A) ##STR9## by decarboxylating to form phenols of theformula (VI A) ##STR10## followed by nitration, to give the nitrocompounds of the formula (VII A) ##STR11## which are then hydrogenated,for example using hydrogen and Raney nickel, to give the correspondingamines of the formula (II A).

The compounds of the formula (VII A) are also a subject of EP-A-No.293,718.

Formula (III) in which X represents cycloalkyl or cycloalkenyl providesa general definition of the cycloalkanecarboxylic acid derivatives orcycloalkenecarboxylic acid derivatives furthermore required for carryingout the process according to the invention. In this formula (III), theradicals X and Hal¹ have the meanings already given in connection withthe description of the compounds of the formula (I) according to theinvention. The compounds are known and can be prepared by analogousprocesses (cf. Diversi et. al., Synthesis 1971, 258; U.S. Pat. No.3,674,831; "Reaktionen der organischen Synthese [Reactions in OrganicSyntheses]", Cesare Ferri, p. 460, 461, 1978, Georg Thieme Verlag,Stuttgart); Houben-Weyl, Methoden der organischen Chemie [Methods ofOrganic Chemistry], Vol. E5, Pt. 1, p. 211, 320, 343, 428 et seq., G.Thieme-Verlag, Stuttgart, 1985).

The carboxylic acid derivatives and carbonic acid derivatives of theformula (V) in which Z and Hal² have the abovementioned meanings, whichare furthermore required for carrying out the process according to theinvention, are known and can be prepared by analogous processes (cf."Reaktion der organischen Synthese [Reaction of Organic Synthesis]"Cesare Ferri, p. 432 et seq., 460 et seq. 1978, Georg Thieme Verlag,Stuttgart; Houben-Weyl, "Methoden der organischen Chemie [Methods ofOrganic Chemistry], Carbonic Acid Derivatives, Vol. E4, p. 9 et seq.,Georg Thieme Verlag, Stuttgart, 1983; Vol. E5 Pt. 1, p. 193 et seq.,Georg Thieme Verlag, Stuttgart, 1985).

Formula (IV) provides a general definition of the acylaminophenols usedas intermediates in the process according to the invention.

New compounds from amongst the compounds of the formula (IV) are thoseof the formula (IVa) ##STR12## in which

X' represents an optionally alkyl-substituted cycloalkenyl radical,preferably a C₁ -C₂ -alkyl-substituted cyclopentenyl, cyclohexenyl orcycloheptenyl radical, and

Y¹, Y², Y³ and Hal have the abovementioned meanings,

The new acylamino derivatives of the formula (IVa) are obtained byreacting aminophenols of the formula (II) ##STR13## in which

Y¹, Y², Y³ and Hal have the abovementioned meanings, with carboxylicacid derivatives of the formula (IIIa) ##STR14## in which

X' and Hal¹ have the abovementioned meanings, if appropriate in thepresence of a solvent and if appropriate in the presence of an acidacceptor.

The remaining compounds of the formula (IV) can be obtainedcorrespondingly or by known processes.

If appropriate, the process according to the invention is carried out inthe presence of acid acceptors. Acid acceptors which can be used are allcustomary acid-binding agents. The following have proved particularlyuseful: alkali metal carbonates and alkali metal alcoholates, such assodium carbonate, potassium carbonate, sodium methylate, potassiummethylate, sodium ethylate or potassium ethylate, furthermore aliphatic,aromatic and heterocyclic amines, for example triethylamine,trimethylamine, dimethylaniline, 1,8-diazobicyclo-(5,4,0)-undec-7-ene,dimethylbenzylamine and pyridine.

For carrying out the process according to the invention, 1-2 moles, inparticular 1-1.4 moles, of the compounds of the general formula (III),or (IIIa), are preferably employed in the first reaction step per moleof amino-phenol of the general formula (II).

In the second reaction step of the process according to the invention,it is preferred to employ 1-2 moles, in particular 1-1.4 moles, of thecompounds of the general formula (V) per mole of a acylaminophenol ofthe formula (IV) or (IVa).

Suitable diluents for carrying out the process according to theinvention are virtually all inert organic diluents. These include, inparticular, aliphatic and aromatic, optionally halogenated hydrocarbons,such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine,ligroin, toluene, xylene, methylene chloride, ethylene chloride,chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene,ethers, such as diethyl ether and dibutyl ether, glycol dimethyl etherand diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones, suchas acetone, methyl ethyl ketone, methyl isopropyl ketone and methylisobutyl ketone, esters, such as methyl acetate and ethyl acetate,nitriles, such as, for example, acetonitrile and propionitrile, amides,such as, for example, dimethylformamide, dimethylacetamide andN-methylpyrrolidone, and also dimethylsulphoxide, tetramethylenesulphone and hexamethylphosphoric triamide.

The process according to the invention is generally carried out attemperatures between -50° C. and 120° C. The range between 0° C. and110° C. is preferred. The reactions are generally carried out underatmospheric pressure.

Working up is carried out by customary methods, for example byextracting the products with toluene or methylene chloride from thereaction mixture which is diluted with water, washing the organic phasewith water, drying and distilling the products, or by so-called"incipient distillation", that is to say, prolonged heating tomoderately increased temperatures under reduced pressure in order tofree the product from the last volatile constituents, or bychromatographic purification via silica gel, or, for example, bycrystallization. The compounds are characterized by the refractiveindex, melting point, R_(f) value or boiling point.

The active compounds according to the invention are suitable for use forcombating pests, in particular as fungicides.

Fungicidal agents in plant protection are employed for combatingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericidal agents are employed in plant protection for combatingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some causative organisms of fungal and bacterial diseases which comeunder the generic names listed above may be mentioned as examples, butnot by way of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example,

Pseudoperonospora humuli or Pseudoperonospora cubense; Plasmoparaspecies, such as, for example, Plasmopara viticola;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Tilletia species, such as, for example, Tilletia caries; Ustilagospecies, such as, for example, Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants, of vegetative propagation stock andseeds, and of the soil.

In this context, the active compounds according to the invention can beemployed with particularly good success for combating Botrytis fungi onbeans and for combating cereal diseases, such as, for example, againstPseudocercosporella.

The active compounds are furthermore suitable for combating animalpests, preferably arthropods and nematodes, in particular insects andarachnids, encountered in agriculture, in forestry, in the protection ofstored products and of materials, and in the hygiene field. They areactive against normally sensitive and resistant species and against allor some stages of development. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp.

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The phytoparasitic nematodes include Pratylenchus spp., Radopholussimilis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heteroderaspp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorusspp., Xiphinema spp. and Trichodorus spp.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, suspensions, powders, foams, pastes,granules, aerosols, very fine capsules in polymeric substances, and incoating compositions for seeds, and also ULV formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is emulsifying agents and/or dispersingagents and/or foam/forming agents. In the case of the use of water as anextender, organic solvents can, for example, also be used as auxiliarysolvents. As liquid solvents, there are suitable in the main: aromatics,such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water. By liquefied gaseous extenders orcarriers are meant liquids which are gaseous at ambient temperature andunder atmospheric pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide. As solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates. Assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,corn cobs and tobacco stalks. As emulsifying and/or foamforming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumin hydrolysis products. Asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in theformulations as a mixture with other known active compounds, such asfungicides, insecticides, acaricides and herbicides, and in mixtureswith fertilizers and other growth regulators.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsifiable concentrates, emulsions, foams, suspensions,wettable powders, pastes, soluble powders, dusts and granules. They areused in the customary manner, for example by watering, spraying,atomizing, scattering, dusting, foaming, brushing on and the like. It isfurthermore possible to apply the active compounds by the ultra-lowvolume method or to inject the active compound formulation or the activecompound itself into the soil. The seed of the plants can also betreated.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001%.

In the treatment of seed, amounts of active compound of 0.001 to 50 gper kilogram of seed, preferably 0.01 to 10 g, are generally required.

For the treatment of soil, active compound concentrations of 0.00001 to0.1% by weight, preferably 0.0001 to 0.02%, are required at the place ofaction.

EXAMPLE 1 ##STR15##

4 g (13.0 mmol) of2,3-dichloro-4-(1-methylcyclohexyl-carbonyl)-amino-phenol are dissolvedin 50 ml of tetrahydrofuran, and 2.5 ml (18.5 mmol) of triethylamine areadded. 1.5 g (14.3 mmol) of methyl chloroformate are subsequently addeddropwise at 20° C. to the reaction mixture. The mixture is stirred for 2hours at 20° C., and the solvent is then distilled off under a waterpump vacuum. The residue which remains is then chromatographed oversilica gel (eluent: petroleum ether: acetone=8:2). Yield: 4.4 g (98% oftheory). M.p.: 125° C.

The following compounds of the formula (I) ##STR16## are preparedanalogously:

    __________________________________________________________________________                                                Physical data                     Example No.                                                                          X           Y.sup.1                                                                         Y.sup.2                                                                         Y.sup.3                                                                         Hal                                                                              Z               (m.p.)                            __________________________________________________________________________     2                                                                                    ##STR17##  Cl                                                                              H H Cl COOCH.sub.2 CH(CH.sub.3).sub.2                                                                109° C.                     3                                                                                    ##STR18##  Cl                                                                              H H Cl COOC.sub.3 H.sub.7 n                                                                          122° C.                     4                                                                                    ##STR19##  Cl                                                                              H H Cl COOCH.sub.2 CH(CH.sub.3)C.sub.2 H.sub.5                                                        67° C.                     5                                                                                    ##STR20##  Cl                                                                              H H Cl                                                                                ##STR21##       63° C.                     6                                                                                    ##STR22##  Cl                                                                              H H Cl                                                                                ##STR23##       91° C.                     7                                                                                    ##STR24##  Cl                                                                              H H Cl                                                                                ##STR25##      107° C.                     8                                                                                    ##STR26##  Cl                                                                              H H Cl                                                                                ##STR27##      125° C.                     9                                                                                    ##STR28##  Cl                                                                              H H Cl                                                                                ##STR29##      110° C.                    10                                                                                    ##STR30##  Cl                                                                              H H Cl COCH.sub.3      105° C.                    11                                                                                    ##STR31##  Cl                                                                              H H Cl COC.sub.4 H.sub.9 -t                                                                          136° C.                    12                                                                                    ##STR32##  Cl                                                                              H H Cl COCH(C.sub.2 H.sub.5)C.sub.4 H.sub.9 -n                                                        45° C.                    13                                                                                    ##STR33##  Cl                                                                              H H Cl                                                                                ##STR34##       71° C.                    14                                                                                    ##STR35##  Cl                                                                              H H Cl                                                                                ##STR36##      102° C.                    15                                                                                    ##STR37##  Cl                                                                              H H Cl                                                                                ##STR38##      110° C.                    16                                                                                    ##STR39##  Cl                                                                              H H Cl                                                                                ##STR40##      108° C.                    17                                                                                    ##STR41##  Cl                                                                              H H Cl                                                                                ##STR42##       66° C.                    18                                                                                    ##STR43##  Cl                                                                              H H Cl                                                                                ##STR44##       90° C.                    19                                                                                    ##STR45##  Cl                                                                              H H Cl                                                                                ##STR46##      145° C.                    20                                                                                    ##STR47##  Cl                                                                              H H Cl                                                                                ##STR48##      104° C.                    21                                                                                    ##STR49##  Cl                                                                              H H Cl                                                                                ##STR50##       82° C.                    22                                                                                    ##STR51##  Cl                                                                              H H Cl                                                                                ##STR52##      128° C.                    23                                                                                    ##STR53##  Cl                                                                              H H Cl                                                                                ##STR54##      122° C.                    24                                                                                    ##STR55##  Cl                                                                              H H Cl                                                                                ##STR56##       93° C.                    25                                                                                    ##STR57##  F F F Cl                                                                                ##STR58##       35° C.                    26                                                                                    ##STR59##  Cl                                                                              H H Cl COOCH.sub.3                                       27                                                                                    ##STR60##  Cl                                                                              H H Cl COOCH.sub.3                                       28                                                                                    ##STR61##  Cl                                                                              H H Cl COOCH.sub.3                                       29                                                                                    ##STR62##  Cl                                                                              H H Cl COOCH.sub.3                                       30                                                                                    ##STR63##  Cl                                                                              H H Cl                                                                                ##STR64##                                        31                                                                                    ##STR65##  Cl                                                                              H H Cl                                                                                ##STR66##                                        32                                                                                    ##STR67##  Cl                                                                              H H Cl                                                                                ##STR68##                                        33                                                                                    ##STR69##  Cl                                                                              H H Cl                                                                                ##STR70##       72° C.                    34                                                                                    ##STR71##  H Cl                                                                              H Cl COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             35                                                                                    ##STR72##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                          52° C.                    36                                                                                    ##STR73##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OCH.sub.3                    37                                                                                    ##STR74##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OC.sub.3 H.sub.7 -i          38                                                                                    ##STR75##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OC.sub.4 H.sub.9 -n          39                                                                                    ##STR76##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OCH(CH.sub.3)C.sub.2                                     H.sub.5                                           40                                                                                    ##STR77##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OC.sub.3 H.sub.7 -n          41                                                                                    ##STR78##  Cl                                                                              H H Cl COOCH.sub.2 CH(CH.sub.3)OCH.sub.3                 42                                                                                    ##STR79##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                       OC.sub.2 H.sub.5                                                                              n.sub.D.sup.20 1.5116             43                                                                                    ##STR80##  Cl                                                                              H H Cl COOCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             __________________________________________________________________________

PREPARATION EXAMPLES

Preparation of the starting compounds:

EXAMPLE A1 ##STR81##

18.5 g (0.085 mol) of 4-amino-2,6-dichlorophenol are dissolved in 150 mlof tetrahydrofuran, and first 8.6 g (0.085 mol) of triethylamine andthen, at 0° C. internal temperature, 15 g (0.094 mol) of1-methylcyclohexanecarboxylic acid chloride are added. The mixture isstirred overnight at 20° C., and another 5 g of carboxylic acid chlorideand 2.8 g of triethylamine are then added to the reaction mixture inorder to complete the reaction. After 2 hours, the mixture is pouredonto ice, and the solid which is filtered off with suction isrecrystallized from toluene. The abovementioned compound of meltingpoint 140° C. is obtained; yield: 22.3 g (=87% of theory).

The compounds of the formula (IV) and (IVa), respectively, are obtainedanalogously:

EXAMPLE A2

3,5-Dichloro-2,6-difluoro-4-hydroxybenzoic acid

300 g of potassium hydroxide, 600 ml of water, 15 g oftetrabutylammonium chloride and 135 g of3,5-dichloro-2,4,6-trifluorobenzotrifluoride are initially introducedinto a stirred vessel, and the mixture is then refluxed for 5 hours.After the reaction has finished, the mixture is cooled and rendered acidby dropwise addition of hydrochloric acid. The solid is filtered offwith suction and dried in vacuo. Yield: 93 g, having a melting point of102°-105° C.

EXAMPLE A3

3-Chloro-2,5,6-trifluoro-4-hydroxy-benzoic acid

Analogously to Example A1, 400 g of NaOH, 1,200 ml of water, 15 g oftetraethylammonium chloride and 276 g of3-chlorotetrafluorobenzotrifluoride, refluxed for 6 hours, give 238 g ofproduct having a melting point of 87°-90° C.

EXAMPLE A4

2,6-Dichloro-3,5-difluorophenol

50 g of 3,5-dichloro-2,6-difluoro-4-hydroxybenzoic acid and 10 ml ofdimethylformamide are mixed, and the mixture is heated. Carbon dioxideis evolved at 105°-130° C., and the mixture is allowed to react at thistemperature until the reaction is complete. After this, 200 ml oftoluene and then 80 ml of water are stirred in, the phases areseparated, and the organic phase is dried and then distilled. This gives34 g of the product having a boiling point of 87°-88° C. and arefractive index of [n]_(D) ²⁰ : 1.5310.

EXAMPLE A5

Analogously to Example A3, 2-chloro-3,5,6-trifluorophenol is obtained,having a boiling point of 68°-70° C./20 mbar.

EXAMPLE A6

2,6-Dichloro-3,5-difluoro-4-nitrophenol

20 g of 2,6-dichloro-3,5-difluorophenol are initially introduced in 70ml of acetic acid, and 8 g of 98% strength nitric acid are addeddropwise. Stirring is subsequently continued at room temperature for 2hours, and the mixture is taken up in 150 ml of dichloromethane andwashed twice with water. After the dichloromethane has been distilledoff, 18 g of product remain. Purity 94% according to GC analysis.

EXAMPLE A7

2-Chloro-3,5,6-trifluoro-4-nitrophenol

Analogously to Example A5, nitration of 28 g of2-chloro-3,5,6-trifluorophenol gives 25 g of2-chloro-3,5,6-trifluoro-4-nitrophenol, having a purity of 93% and amelting point of 107°-109° C.

EXAMPLE A8

2,6-Dichloro-3,5-difluoro-4-amino-phenol

18 g of 2,6-dichloro-3,5-difluoro-4-nitrophenol are hydrogenated in 100ml of methanol in the presence of 1.5 g of Raney nickel at 25°-45° C.and 30-50 bar of hydrogen until hydrogen is no longer taken up. Themixture is filtered, and the solution is then freed from the solventunder reduced pressure. 13 g of aminophenol remain (GC purity 98.4%);m.p. 151° C.

EXAMPLE A9

2-Chloro-3,5,6-trifluoro-4-amino-phenol

Analogously to Example A7, hydrogenation of 25 g of2-chloro-3,5,6-trifluoro-4-nitro-phenol in 120 ml of methanol and 2 g ofRaney nickel gives 20 g of aminophenol (GC purity 97%).

Analogously to Example A1, the following compounds of the formula (IVA)are obtained.

    ______________________________________                                         ##STR82##                   (IVa)                                            Ex. No.                                                                              X'               Y.sup.1                                                                             Y.sup.2                                                                             Y.sup.3                                                                           Hal                                   ______________________________________                                        A11                                                                                   ##STR83##       Cl    H     H   Cl                                    A12                                                                                   ##STR84##       Cl    H     Cl  H                                     A13                                                                                   ##STR85##       Cl    H     H   Cl                                    A14                                                                                   ##STR86##       Cl    H     Cl  H                                     A15                                                                                   ##STR87##       Cl    H     Cl  H                                     A16                                                                                   ##STR88##       Cl    H     H   Cl                                    ______________________________________                                    

EXAMPLE

Botrytis test (bean)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, 2 small pieces of agar covered with Botrytiscinerea are placed on each leaf. The inoculated plants are placed in adarkened humid chamber at 20° C. 3 days after the inoculation, the sizeof the infected spots on the leaves is evaluated.

In this test, a clearly high activity is shown, for example, by thecompounds of the following Preparation Examples: 1, 2, 3, 4, 6, 7, 8, 9,35 and 42.

It is understood that the specification and examples are illustrativebut not limitative of the present invention and that other embodimentswithin the spirit and scope of the invention will suggest themselves tothose skilled in the art.

We claim:
 1. A cycloalkyl- or cycloalkenyl-carboxanilide of the formula##STR89## X represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexylor cycloheptyl, each of which is optionally monosubstituted totetrasubstituted by identical or different substituents from the groupconsisting of straight-chain or branched alkyl radicals having 1-4carbon atoms, or represents cycloalkenyl having 5-7 ring members andoptionally monosubstituted to hexasubstituted by identical or differentsubstituents from the group consisting of straight-chain and branchedalkyl radicals having 1-4 carbon atoms,Hal represents fluorine, chlorineor bromine, Y¹ Y² and Y³ are identical or different and representhydrogen, fluorine, chlorine, bromine, straight-chain or branched alkylhaving 1-4 carbon atoms, straight-chain or branched alkoxy or alkylthioeach having 1-4 carbon atoms, or represent halogenoalkyl, halogenoalkoxyor halogenoalkylthio each having 1-4 carbon atoms in the straight-chainor branched alkyl moiety and having 1-5 identical or different halogenatoms, Z represents COOR², where R² represents C₁₋₈ -alkyl, C₂₋₈-alkenyl, C₁₋₄ -alkoxy-C₁₋₄ -alkyl, C₁₋₄ -alkoxy-C₁₋₄ -alkoxy-C₁₋₄-alkyl or C₁₋₄ -alkylthio-C₁₋₄ -alkyl, each of which is optionallymonosubstituted to nonasubstituted by halogen, or represents C₃₋₇-cycloalkyl which is unsubstituted or monosubstituted topentasubstituted by identical or different substituents from the groupconsisting of C₁₋₄ -halogenoalkyl, halogen, C₁₋₄ -alkyl, C₁₋₄ -alkoxy,hydroxyl and C₁₋₆ -alkylcarbonyloxy, or represents phenyl-C₁₋₄ -alkylwhich is unsubstituted or monosubstituted to pentasubstituted in thephenyl moiety by identical or different substitutents from the groupconsisting of Y¹ '-Y⁵ ', or represents phenoxyalkyl which isunsubstituted or monosubstituted to pentasubstituted in the phenylmoiety by identical or different substituents from the group consistingof Y¹ '-Y⁵ ', where Y¹ '-Y⁵ ' have the meaning of Y¹ -Y³, NO₂ and cyano.2. A compound according to claim 1, in whichX represents cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, each of which ismonosubstituted or disubstituted by identical or different substituentsfrom the group consisting of straight-chain or branched alkyl radicalshaving 1-4 carbon atoms, or represents cyclopentenyl, cyclohexenyl orcycloheptenyl, each of which is optionally monosubstituted ordisubstituted by identical or different substituents from the groupconsisting of straight-chain and branched alkyl radicals having 1-4carbon atoms, Y¹, Y² and Y³ identical or different and representhydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl, andHal represents fluorine, chlorine or bromine, Z represents COOR², whereR² represents C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₁ -C₄ -alkoxy-C₁ -C₄-alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl or C₁ -C₄-alkylthio-C₁ -C₂ -alkyl, or represents C₃ -C₇ -cycloalkyl which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents from the group consisting of fluorine, chlorine,bromine, C₁ -C₂ -alkyl, C₁ -C₂ -alkoxy and C₁ -C₆ -alkylcarbonyloxy, orrepresent phenyl which is unsubstituted or monosubstituted totrisubstituted by identical or different substituents from the groupconsisting of nitro, cyano, fluorine, chlorine, bromine, methyl,trifluoromethyl, trifluoromethylthio, methoxy and trifluoromethoxy, orrepresents phenyl-C₁ -C₂ -alkyl which is unsubstituted ormonosubstituted to trisubstituted by identical or different substituentsfrom the group consisting of nitro, cyano, fluorine, chlorine, bromine,methyl, trifluoromethyl, trifluoromethylthio, methoxy andtrifluoromethoxy, or represents phenoxy-C₁ -C₂ -alkyl which isunsubstituted or monosubstituted to trisubstituted by identical ordifferent substituents from the group consisting of nitro, cyano,fluorine, chlorine, bromine, methyl, trifluoromethyl,trifluoromethylthio, methoxy and trifluoromethoxy.
 3. A compoundaccording to claim 1, in whichX represents cyclopentyl, cyclohexyl,cycloheptyl, cyclopentenyl, cyclohexenyl or cycloheptenyl, each of whichis substituted in the 1- or 1,3-position by methyl or ethyl and each ofwhich is optionally additionally substituted by a further alkyl radicalhaving 1-3 carbon atoms, Hal represents fluorine, chlorine or bromine,and Y¹, Y² and Y³ are identical or different and represent hydrogen,fluorine, chlorine, bromine or trifluoromethyl, Z represents COOR² orCOR¹, where R² represents C₁ -C₄ -alkyl, C₂ -C₅ -alkenyl, C₁ -C₄-alkoxy-C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy-C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, orrepresents C₃ -C₇ -cycloalkyl which is monosubstituted to trisubstitutedby identical or different substituents from the group consisting ofmethoxy, fluorine, chlorine, bromine, methyl and C₁ -C₄-alkylcarbonyloxy, or represents phenyl which is monosubstituted totrisubstituted by identical or different substituents from the groupconsisting of nitro, cyano, fluorine, chlorine, bromine, methyl andmethoxy, or represents phenylmethyl which is monosubstituted totrisubstituted by identical or different substituents from the groupconsisting of nitro, cyano, fluorine, chlorine, bromine, methyl andmethoxy.
 4. The compound according to claim 1, wherein such compound is2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylmethylcarbonate of the formula ##STR90##
 5. The compound according toclaim 1, which is2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylisobutylcarbonate of the formula ##STR91##
 6. The compound according toclaim 1, which is2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenyln-propylcarbonate of the formula ##STR92##
 7. The compound according toclaim 1, which is2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenyl2-methyl-butyl-carbonate of the formula ##STR93##
 8. A fungicidalcomposition comprising a fungicidally effective amount of a compoundaccording to claim 1 and a diluent.
 9. A method of combating fungi whichcomprises applying to the fungi or to a locus from which it is desiredto exclude the fungi a fungicidally effective amount of a compoundaccording to claim
 1. 10. The method according to claim 9, wherein suchcompound is2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylmethylcarbonate, 2.3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylisobutylcarbonate,2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenyln-propylcarbonate,2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenyl2-methyl-butyl-carbonate,2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylethoxyethylcarbonate or2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylethoxyethoxyethylcarbonate.
 11. A compound according to claim 1, whereinsuch compound is2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylethoxyethylcarbonate of the formula ##STR94##
 12. A compound accordingto claim 1, wherein such compound is2,3-dichloro-4-(1-methyl-cyclohexyl-carbonyl)-amino-phenylethoxyethoxyethylcarbonate of the formula ##STR95##